Diversity oriented synthesis of chromene-xanthene hybrids as anti-breast cancer agents

被引：32

作者：

Kumar, M. Srinivas Lavanya ^{[1
]}

Singh, Jyotsana ^{[3
]}

Manna, Sudipta Kumar ^{[1
,4
]}

Maji, Saroj ^{[1
]}

Konwar, Rituraj ^{[2
]}

Panda, Gautam ^{[1
,2
]}

机构：

[1] CSIR, Cent Drug Res Inst, BS 10-1,Sect 10,Sitapur Rd, Lucknow 226031, Uttar Pradesh, India

[2] Acad Sci & Innovat Res, New Delhi 110001, India

[3] CSIR, Cent Drug Res Inst, Endocrinol Div, Sect 10,Sitapur Rd, Lucknow 226031, Uttar Pradesh, India

[4] Nagoya Univ, Res Ctr Mat Sci, Dept Chem, Chikusa Ku, Nagoya, Aichi 4648602, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2018年 / 28卷 / 04期

关键词：

Synthesis; Anti-cancer; Hybrid; Chromene; SOLID-PHASE SYNTHESIS; PRIVILEGED STRUCTURES; CYTOTOXIC ACTIVITY; DRUG DISCOVERY; DERIVATIVES; ANALOGS; LIBRARIES; IDENTIFICATION; CONSTRUCTION; PERSPECTIVES;

D O I：

10.1016/j.bmcl.2017.12.065

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A diverse library of chromene-xanthene hybrids were synthesized through intramolecular Friedel-Crafts reaction of the arenoxy carbinols. Examples include first incorporation of amino acid tyrosine into xanthene skeletons with polar functionalities. A careful structural evaluation revealed that tyrosine crafted chromene-xanthene hybrids exhibited good activities against breast cancer cell lines MCF-7, MDA-MB-231. The lead compound 16 displays significant cell cycle arrest at G1 phase and induces apoptosis in MDA-MB-231 cells. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：778 / 782

页数：5

共 40 条

[1]

Anders A., 2009, J MED CHEM, V52, P912, DOI DOI 10.1021/JM8013458

[2]

[Anonymous], 1992, The Production and Application of Fluorescent Brightening Agents

[3] A rapid entry to amino acid derived diverse 3,4-dihydropyrazines and dihydro[1,2,3]triazolo[1,5-a]-pyrazines through 1,3-dipolar cycloaddition [J].

Bera, Saurav ;

Panda, Gautam .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (23) :3976-3985

[4] SYNTHESIS AND PHARMACOLOGICAL ACTIVITY OF 2-OXO-(2H) 1-BENZOPYRAN-3-CARBOXAMIDE DERIVATIVES [J].

BONSIGNORE, L ;

LOY, G ;

SECCI, D ;

CALIGNANO, A .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1993, 28 (06) :517-520

[5] Synthesis, Cytotoxic Activity, and Mechanism of Action of Furo[2,3-c]acridin-6-one and Benzo[b]furo[3,2-h]acridin-6-one Analogues of Psorospermin and Acronycine [J].

Boutefnouchet, Sabrina ;

Gaboriaud-Kolar, Nicolas ;

Minh, Nguyen Tuan ;

Depauw, Sabine ;

David-Cordonnier, Marie-Helene ;

Pfeiffer, Bruno ;

Leonce, Stephane ;

Pierre, Alain ;

Tillequin, Francois ;

Lallemand, Marie-Christine ;

Michel, Sylvie .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (22) :7287-7297

[6] A New Synthetic Route to Unsymmetrical 9-Arylxanthenes [J].

Das, Sajal Kumar ;

Singh, Ritesh ;

Panda, Gautam .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (28) :4757-4761

[7] Hybrid Molecules Incorporating Natural Products: Applications in Cancer Therapy, Neurodegenerative Disorders and Beyond [J].

Decker, M. .

CURRENT MEDICINAL CHEMISTRY, 2011, 18 (10) :1464-1475

[8] Privileged structures: Applications in drug discovery [J].

DeSimone, RW ;

Currie, KS ;

Mitchell, SA ;

Darrow, JW ;

Pippin, DA .

COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING, 2004, 7 (05) :473-493

[9] Identification of chemically diverse Chk1 inhibitors by receptor-based virtual screening [J].

Foloppe, Nicolas ;

Fisher, Lisa M. ;

Howes, Rob ;

Potter, Andrew ;

Robertson, Alan G. S. ;

Surgenor, Allan E. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (14) :4792-4802

[10] Design, synthesis, and biological evaluation of cytotoxic 11-alkenylindenoisoquinoline topoisomerase I inhibitors and indenoisoquinoline-Camptothecin hybrids [J].

Fox, BM ;

Xiao, XS ;

Antony, S ;

Kohlhagen, G ;

Pommier, Y ;

Staker, BL ;

Stewart, L ;

Cushman, M .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (15) :3275-3282

← 1 2 3 4 →